Anthracene derivatives and organic electronic device using the same

ABSTRACT

The present invention relates to a novel anthracene derivative and an organic electronic device using the same. The organic electronic device according to the present invention shows excellent characteristics in efficiency, driving voltage, and life time.

TECHNICAL FIELD

The present invention relates to a novel anthracene derivative having apyridyl group bonded to anthracene, and to an organic electronic deviceusing the same.

This application claims priority from Korean Patent Application No.10-2007-48158 filed on May 17, 2007 in the KIPO, the disclosure of whichis incorporated herein by reference in its entirety.

BACKGROUND ART

The term, organic electronic device, as used in the presentspecification refers to a device using an organic semiconductormaterial, which requires hole and/or electron exchange between anelectrode and an organic semiconductor material. The organic electronicdevice can be largely classified into two types according to itsoperational principle as follows. One type is an electronic devicehaving a configuration in which an exciton is formed in an organicmaterial layer by photons flown from an external light source into thedevice and the exciton is separated into an electron and a hole, theelectron and the hole formed are transported to a different electrode,respectively and used as a current source (voltage source), and theother type is an electronic device having a configuration in which holesand/or electrons are injected into an organic material semiconductorforming an interface with an electrode by applying a voltage or currentto two or more electrodes to allow the device to operate by means of theinjected electron and hole.

Examples of the organic electronic device include an organic lightemitting device, an organic solar cell, an organic photoconductor (OPC)drum and an organic transistor, which all require an electron/holeinjecting material, an electron/hole extracting material, anelectron/hole transporting material, or a light emitting material fordriving the device. Hereinafter, the organic light emitting device willbe mainly and specifically described, but in the above-mentioned organicelectronic devices, the electron/hole injecting material, theelectron/hole extracting material, the electron/hole transportingmaterial or the light emitting material injection functions according toa similar principle.

In general, the term “organic light emitting phenomenon” refers to aphenomenon in which electric energy is converted to light energy bymeans of an organic material. The organic light emitting device usingthe organic light emitting phenomenon has a structure usually comprisingan anode, a cathode and an organic material layer interposedtherebetween. Herein, the organic material layer may be mostly formed ina multilayer structure comprising layers of different materials, forexample, the hole injecting layer, the hole transporting layer, thelight emitting layer, the electron transporting layer, the electroninjecting layer and the like, in order to improve efficiency andstability of the organic light emitting device. In the organic lightemitting device having such a structure, when a voltage is appliedbetween two electrodes, holes from the anode and electrons from acathode are injected into the organic material layer, the holes and theelectrons injected are combined together to form excitons. Further, whenthe excitons drop to a ground state, lights are emitted. Such theorganic light emitting device is known to have characteristics such asself-luminescence, high brightness, high efficiency, low drive voltage,wide viewing angle, high contrast and high-speed response.

The materials used for the organic material layer of the organic lightemitting device can be classified into a light emitting material and acharge-transporting material, for example, a hole injecting material, ahole transporting material, an electron transporting material and anelectron injecting material, according to their functions. The lightemitting materials can be divided into a blue, green or red lightemitting material and a yellow or orange light emitting materialrequired for giving more natural color, according to a light emittingcolor. Further, a host/dopant system can be used as the light emittingmaterial for the purpose of enhancing the color purity and the lightemitting efficiency through energy transfer. It is based on theprinciple that if a small amount of a dopant having a smaller energyband gap than a host which forms a light emitting layer, excitons whichare generated in the light emitting layer are transported to the dopant,thus emitting a light having a high efficiency. Here, since thewavelength of the host is moved according to the wavelength of thedopant, a light having a desired wavelength can be obtained accordingthe kind of the dopant.

In order to allow the organic light emitting device to fully exhibit theabove-mentioned excellent characteristics, a material constituting theorganic material layer in the device, for example, a hole injectingmaterial, a hole transporting material, a light emitting material, anelectron transporting material and an electron injecting material shouldbe essentially composed of a stable and efficient material. However, thedevelopment of a stable and efficient organic material layer materialfor the organic light emitting device has not yet been fully realized.Accordingly, the development of new materials is continuously desired.

DISCLOSURE Technical Problem

The present inventors have synthesized an anthracene derivative having anovel structure, and then have found that the novel anthracenederivative having a pyridyl group bonded to anthracene can exhibiteffects of increased efficiency, lower voltage and higher stability of adevice when it is used to form an organic material layer of the organicelectronic device. In addition, the present inventors have found that inthe case both an amino group and a pyridyl group are present like theanthracene derivative, an electron injecting ability is increased ascompared to the case that both the groups are not present, thussignificantly reducing driving voltage and increasing efficiency.

Therefore, it is an object of the present invention to provide a novelanthracene derivative having a pyridyl group bonded to anthracene and anorganic electronic device using the same.

Technical Solution

The present invention provides an anthracene derivative that isrepresented by the following formula 1:

wherein R1 and R2 may be the same as or different from each other, andare independently selected from the group consisting of a C₆ to C₄₀ arylgroup which is unsubstituted or substituted with at least one selectedfrom the group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C₆ to C₄₀ aryl group, a C₃ to C₄₀ heteroarylgroup and an arylamine group; a C₃ to C₄₀ heteroaryl group which isunsubstituted or substituted with at least one selected from the groupconsisting of halogen, an amino group, a nitrile group, a nitro group, aC₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxygroup, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group,a C₆ to C₄₀ aryl group and a C₃ to C₄₀ heteroaryl group; and a C₆ to C₄₀amino group which is unsubstituted or substituted with at least oneselected from the group consisting of halogen, an amino group, a nitrilegroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₁ to C₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ toC₄₀ heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group,

at least one of R3 and R4 is represented by the following formula 2:

wherein X is selected from the group consisting of N, P and P═O,

Y is selected from the group consisting of C—H and N,

L₁ is a direct bond; or is selected from the group consisting of a C₂ toC₄₀ alkenylene group which is unsubstituted or substituted with at leastone selected from the group consisting of a C₁ to C₄₀ alkyl group, a C₂to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₁ to C₄₀ alkoxygroup, a C₆ to C₄₀ aryl group, and a C₃ to C₄₀ heteroaryl group; a C₆ toC₄₀ arylene group which is unsubstituted or substituted with at leastone selected from the group consisting of halogen, an amino group, anitrile group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, aC₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group; C₅ to C₄₀ heteroarylene group which is unsubstitutedor substituted with at least one selected from the group consisting ofhalogen, an amino group, a nitrile group, a nitro group, a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀aryl group and a C₃ to C₄₀ heteroaryl group; and a C₆ to C₄₀ arylaminegroup which is unsubstituted or substituted with at least one selectedfrom the group consisting of a C₁ to C₄₀ alkyl group, a C₂ to C₄₀alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, aC₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group,

R5, R6, R7, R8, R9, R10, R11, and R12 may be the same as or differentfrom each other, and are selected from the group consisting of hydrogen;a silicon group which is unsubstituted or substituted with at least oneselected from the group consisting of halogen, an amino group, a nitrilegroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₁ to C₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ toC₄₀ heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group; a C₁ to C₄₀ alkyl group which is unsubstituted orsubstituted with at least one selected from the group consisting ofhalogen, an amino group, a nitrile group, a nitro group, a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀aryl group and a C₃ to C₄₀ heteroaryl group; a C₃ to C₄₀ cycloalkylgroup which is unsubstituted or substituted with at least one selectedfrom the group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group; a C₂ to C₄₀ alkenyl group which is unsubstituted orsubstituted with at least one selected from the group consisting ofhalogen, an amino group, a nitrile group, a nitro group, a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀aryl group and a C₃ to C₄₀ heteroaryl group; a C₁ to C₄₀ alkoxy groupwhich is unsubstituted or substituted with at least one selected fromthe group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group; an amino group which is unsubstituted or substitutedwith at least one selected from the group consisting of halogen, anamino group, a nitrile group, a nitro group, a C₁ to C₄₀ alkyl group, aC₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃ to C₄₀cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀ arylgroup and a C₃ to C₄₀ heteroaryl group; a C₆ to C₄₀ aryl group which isunsubstituted or substituted with at least one selected from the groupconsisting of halogen, an amino group, a nitrile group, a nitro group, aC₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxygroup, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group,a C₆ to C₄₀ aryl group and a C₃ to C₄₀ heteroaryl group; and a C₃ to C₄₀heteroaryl group which is unsubstituted or substituted with at least oneselected from the group consisting of halogen, an amino group, a nitrilegroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₁ to C₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ toC₄₀ heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group, or are bonded with an adjacent group to form analiphatic, aromatic, heteroaliphatic, or heteroaromatic condensed ring,or to form a spiro bond, and

when any one of R3 and R4 is represented by formula 2, the other isselected from the group consisting of hydrogen; a C₆ to C₄₀ aryl groupwhich is unsubstituted or substituted with at least one selected fromthe group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C_(s) to C₄₀ aryl group, a C₃ to C₄₀heteroaryl group and an arylamine group; a C₃ to C₄₀ heteroaryl groupwhich is unsubstituted or substituted with at least one selected fromthe group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group; and a C₆ to C₄₀ amino group which is unsubstituted orsubstituted with at least one selected from the group consisting ofhalogen, an amino group, a nitrile group, a nitro group, a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀aryl group and a C₃ to C₄₀ heteroaryl group.

In an embodiment of the present invention, R1 and R2 of formula 1 may bethe same aryl groups. It is preferable that the aryl groups be thesubstituted or unsubstituted phenyl group, biphenyl group or naphthylgroup.

In another embodiment of the present invention, R1 and R2 of formula 1may be the same heteroaryl groups. It is preferable that the heteroarylgroups be the substituted or unsubstituted pyridyl group, bipyridylgroup, quinolyl group or isoquinolyl group.

In still another embodiment of the present invention, R1 and R2 offormula 1 may be the amino groups substituted with the same C₆˜C₄₀ arylgroups or the same C₃˜C₄₀ heteroaryl groups.

In a further embodiment of the present invention, R1 and R2 of formula 1may be specifically selected from the group consisting of the followingstructural formulas:

wherein Z1 to Z3 are the same as or different from each other, and maybe independently hydrogen or selected from the groups defined inrespects to R1 and R2 of formula 1.

In a yet another embodiment of the present invention, in formula 2, itis preferable that L₁ be a direct bond, an unsubstituted C₆˜C₄₀ arylenegroup, or an unsubstituted C₅˜C₄₀ heteroarylene group.

ADVANTAGEOUS EFFECTS

The novel anthracene compound according to the present invention can beused as a material for an organic material layer of an organicelectronic device including an organic light emitting device by theintroduction of a pyridyl derivative to the anthracene compound. Theorganic electronic device including an organic light emitting device,which uses the anthracene compound according to the present invention asa material for an organic material layer, shows significantly reduceddriving voltage and excellent characteristics in efficiency, life time,or the like.

DESCRIPTION OF DRAWINGS

FIG. 1 illustrates an example of an organic light emitting deviceaccording to the present invention.

NUMERAL REFERENCES

-   -   1. substrate    -   2. anode    -   3. hole injecting layer    -   4. hole transporting layer    -   5. organic light emitting layer    -   6. electron transporting layer    -   7. cathode

BEST MODE

Substituent groups will be described in detail.

The alkyl group is preferably one having 1 to 40 carbon atoms, whichdoes not give steric hindrance. Specific examples thereof include, butnot limited thereto, a methyl group, an ethyl group, a propyl group, anisopropyl group, a butyl group, a t-butyl group, a pentyl group, a hexylgroup and a heptyl group.

The cycloalkyl group is preferably a cycloalkyl group having 3 to 40carbon atoms, which does not give steric hindrance. More preferablespecific examples thereof include a cyclopentyl group and a cyclohexylgroup.

The alkenyl group is preferably an alkenyl group having 2 to 40 carbonatoms, and specifically it is one substituted with an aryl group such asa stilbenzyl group and a styrenyl group.

The alkoxy group is preferably an alkoxy group having 1 to 40 carbonatoms.

Examples of the aryl group include a phenyl group, a naphthyl group, ananthracenyl group, a biphenyl group, a pyrenyl group, a perylenyl group,and a derivative thereof, but are not limited thereto.

Examples of the arylamine group include a phenylamine group, anaphthylamine group, a biphenylamine group, an anthracenylamine group, a3-methyl-phenylamine group, a 4-methyl-naphthylamine group, a2-methyl-biphenylamine group, a 9-methyl-anthracenylamine group, adiphenylamine group, a phenylnaphthylamine group, a ditolylamine group,a phenyltolylamine group, a carbazole group and a triphenylamine group,but are not limited thereto.

Examples of the heterocyclic group include a pyridyl group, a bipyridylgroup, a triazine group, an acridyl group, a thiophene group, a purangroup, an imidazole group, an oxazole group, a thiazole group, atriazole group, a quinolinyl group, and an isoquinoline group, but arenot limited thereto.

Examples of halogen include fluorine, chlorine, bromine, and iodine.

In the present specification, the term “adjacent group” means asubstituent group that is adjacent to the corresponding substituentgroup, and the adjacent substituent group includes a hydrogen atom thatis not represented by Formula.

If the C₂ to C₄₀ alkenylene group is substituted, the substituent is atleast one selected from the group consisting of a substituted orunsubstituted C₁ to C₄₀ alkyl group, a substituted or unsubstituted C₂to C₄₀ alkenyl group, a substituted or unsubstituted C₂ to C₄₀ alkynylgroup, a substituted or unsubstituted C₁ to C₄₀ alkoxy group, asubstituted or unsubstituted C₆ to C₄₀ aryl group, and a substituted orunsubstituted C₃ to C₄₀ heteroaryl group.

Preferable specific examples of the compound of formula 1 include thefollowings, but not limited thereto.

TABLE 1

Formula R1 R2 L₁ Ar₁ 1-1

direct bond

1-2

direct bond

1-3

direct bond

1-4

direct bond

1-5

direct bond

1-6

direct bond

1-7

direct bond

1-8

direct bond

1-9

direct bond

1-10

direct bond

1-11

direct bond

1-12

direct bond

1-13

direct bond

1-14

direct bond

1-15

direct bond

1-16

direct bond

1-17

direct bond

1-18

direct bond

1-19

direct bond

1-20

direct bond

1-21

direct bond

1-22

direct bond

1-23

direct bond

1-24

direct bond

1-25

direct bond

1-26

direct bond

1-27

direct bond

1-28

direct bond

1-29

direct bond

1-30

direct bond

1-31

direct bond

1-32

direct bond

1-33

direct bond

1-34

direct bond

1-35

direct bond

1-36

direct bond

1-37

direct bond

1-38

direct bond

1-39

direct bond

1-40

direct bond

1-41

direct bond

1-42

direct bond

1-43

direct bond

1-44

direct bond

1-45

direct bond

1-46

direct bond

1-47

direct bond

1-48

direct bond

1-49

direct bond

1-50

direct bond

1-51

direct bond

1-52

direct bond

1-53

direct bond

1-54

direct bond

1-55

direct bond

1-56

direct bond

1-57

direct bond

1-58

direct bond

1-59

direct bond

1-60

direct bond

1-61

direct bond

1-62

direct bond

1-63

direct bond

1-64

direct bond

1-65

direct bond

1-66

direct bond

1-67

direct bond

1-68

direct bond

1-69

direct bond

1-70

direct bond

1-71

direct bond

1-72

direct bond

1-73

direct bond

1-74

direct bond

1-75

direct bond

1-76

direct bond

1-77

direct bond

1-78

direct bond

1-79

direct bond

1-80

direct bond

1-81

direct bond

1-82

direct bond

1-83

direct bond

1-84

direct bond

1-85

direct bond

1-86

direct bond

1-87

direct bond

1-88

direct bond

1-89

direct bond

1-90

direct bond

1-91

1-92

1-93

1-94

1-95

1-96

1-97

1-98

1-99

1-100

1-101

1-102

1-103

1-104

1-105

1-106

1-107

1-108

1-109

1-110

1-111

1-112

1-113

1-114

1-115

1-116

1-117

1-118

1-119

1-120

1-121

1-122

1-123

1-124

1-125

1-126

1-127

1-128

1-129

1-130

1-131

1-132

1-133

1-134

1-135

1-136

1-137

1-138

1-139

1-140

1-141

1-142

1-143

1-144

1-145

1-146

1-147

1-148

1-149

1-150

1-151

1-152

1-153

1-154

1-155

1-156

1-157

1-158

1-159

1-160

1-161

1-162

1-163

1-164

1-165

1-166

1-167

1-168

1-169

1-170

1-171

1-172

1-173

1-174

1-175

1-176

1-177

1-178

1-179

1-180

1-181

1-182

1-183

1-184

1-185

1-186

1-187

1-188

1-189

1-190

1-191

1-192

1-193

1-194

1-195

1-196

1-197

1-198

1-199

1-200

1-201

1-202

1-203

1-204

1-205

1-206

1-207

1-208

1-209

1-210

1-211

1-212

1-213

1-214

1-215

1-216

1-217

1-218

1-219

1-220

1-221

1-222

1-223

1-224

1-225

1-226

1-227

1-228

1-229

1-230

1-231

1-232

1-233

1-234

1-235

1-236

1-237

1-238

1-239

1-240

1-241

1-242

1-243

1-244

1-245

1-246

1-247

1-248

1-249

1-250

1-251

1-252

1-253

1-254

1-255

1-256

1-257

1-258

1-259

1-260

1-261

1-262

1-263

1-264

1-265

1-266

1-267

1-268

1-269

1-270

1-271

1-272

1-273

1-274

1-275

1-276

1-277

1-278

1-279

1-280

1-281

1-282

1-283

1-284

1-285

1-286

1-287

1-288

1-289

1-290

1-291

1-292

1-293

1-294

1-295

1-296

1-297

1-298

1-299

1-300

[Compound 1-301] Compound 1-302] Compound 1-303

[Compound 1-304] [Compound 1-305] [Compound 1-306]

[Compound 1-307] [Compound 1-308] [Compound 1-309]

[Compound 1-310] [Compound 1-311] [Compound 1-312]

[Compound 1-313] [Compound 1-314] [Compound 1-315]

[Compound 1-316] [Compound 1-317] [Compound 1-318]

[Compound 1-319] [Compound 1-320] [Compound 1-321]

[Compound 1-322] [Compound 1-323] [Compound 1-324]

TABLE 2

Formula R1 R2 L₁ Ar₁ 2-1

direct bond

2-2

direct bond

2-3

direct bond

2-4

direct bond

2-5

direct bond

2-6

direct bond

2-7

direct bond

2-8

direct bond

2-9

direct bond

2-10

direct bond

2-11

direct bond

2-12

direct bond

2-13

direct bond

2-14

direct bond

2-15

direct bond

2-16

direct bond

2-17

direct bond

2-18

direct bond

2-19

direct bond

2-20

direct bond

2-21

direct bond

2-22

direct bond

2-23

direct bond

2-24

direct bond

2-25

direct bond

2-26

direct bond

2-27

direct bond

2-28

direct bond

2-29

direct bond

2-30

direct bond

2-31

direct bond

2-32

direct bond

2-33

direct bond

2-34

direct bond

2-35

direct bond

2-36

direct bond

2-37

direct bond

2-38

direct bond

2-39

direct bond

2-40

direct bond

2-41

direct bond

2-42

direct bond

2-43

direct bond

2-44

direct bond

2-45

direct bond

2-46

direct bond

2-47

direct bond

2-48

direct bond

2-49

direct bond

2-50

direct bond

2-51

direct bond

2-52

direct bond

2-53

direct bond

2-54

direct bond

2-55

direct bond

2-56

direct bond

2-57

direct bond

2-58

direct bond

2-59

direct bond

2-60

direct bond

2-61

direct bond

2-62

direct bond

2-63

direct bond

2-64

direct bond

2-65

direct bond

2-66

direct bond

2-67

direct bond

2-68

direct bond

2-69

direct bond

2-70

direct bond

2-71

direct bond

2-72

direct bond

2-73

direct bond

2-74

direct bond

2-75

direct bond

2-76

direct bond

2-77

direct bond

2-78

direct bond

2-79

direct bond

2-80

direct bond

2-81

2-82

2-83

2-84

2-85

2-86

2-87

2-88

2-89

2-90

2-91

2-92

2-93

2-94

2-95

2-96

2-97

2-98

2-99

2-100

2-101

2-102

2-103

2-104

2-105

2-106

2-107

2-108

2-109

2-110

2-111

2-112

2-113

2-114

2-115

2-116

2-117

2-118

2-119

2-120

2-121

2-122

2-123

2-124

2-125

2-126

2-127

2-128

2-129

2-130

2-131

2-132

2-133

2-134

2-135

2-136

2-137

2-138

2-139

2-140

2-141

2-142

2-143

2-144

2-145

2-146

2-147

2-148

2-149

2-150

2-151

2-152

2-153

2-154

2-155

2-156

2-157

2-158

2-159

2-160

2-161

2-162

2-163

2-164

2-165

2-166

2-167

2-168

2-169

2-170

2-171

2-172

2-173

2-174

2-175

2-176

2-177

2-178

2-179

2-180

2-181

2-182

2-183

2-184

2-185

2-186

2-187

2-188

2-189

2-190

2-191

2-192

2-193

2-194

2-195

2-196

2-197

2-198

2-199

2-200

2-201

2-202

2-203

2-204

2-205

2-206

2-207

2-208

2-209

2-210

2-211

2-212

2-213

2-214

2-215

2-216

2-217

2-218

2-219

2-220

2-221

2-222

2-223

2-224

2-225

2-226

2-227

2-228

2-229

2-230

2-231

2-232

2-233

2-234

2-235

2-236

2-237

2-238

Hereinbelow, a method for preparing an anthracene derivative that has apyridyl group represented by formula 2 introduced to the compound offormula 1 will be described.

The compound of formula 1 can be prepared by introducing an arylsubstituent to an anthracene derivative. Specifically, the compound offormula 1 can be prepared by subjecting a 2-anthracene boronic acid or2-anthracene boronic ester derivative and an arylhalide derivative orheteroarylhalide derivative to a Suzuki coupling reaction in thepresence of a Pd catalyst.

For the process used for preparation of the compound of formula 1, othergeneral processes known in the art can be used, in addition to theSuzuki coupling reaction.

Specifically, the compound of formula 1 can be prepared by the methodcomprising the steps of:

1) subjecting a halogen-substituted anthraquinone derivative and aboronic acid or boronic ester compound having a R4 substituent to Suzukicoupling in the presence of a Pd catalyst to prepare a R4-substitutedanthraquinone derivative,

2) preparing a dialcohol derivative from the anthraquinone derivativeprepared in the step 1), and

3) reducing the dialcohol derivative prepared in the step 2) to preparedan anthracene derivative. This preparation method can be represented byeach of Reaction scheme 1.

Further, the compound of formula 1 can be prepared by the methodcomprising the steps of:

1) preparing a dialcohol derivative from a halogen-substitutedanthraquinone derivative,

2) reducing the dialcohol derivative prepared in the step 1) to preparedan anthracene derivative,

3) preparing an anthracene boronic ester derivative from an anthracenederivative prepared in the step 2), and

4) subject the anthracene boronic ester derivative prepared in the step3) and a halide of R4 to Suzuki coupling in the presence of a Pdcatalyst to prepare a R4-substituted compound of formula 1. Thispreparation method can be represented by each of Reaction scheme 2.

Specifically, the substituent group of formula 2 can be prepared by themethod comprising the steps of:

1) reacting the pyridyl derivative in which a halogen group issubstituted with a substance which is substituted with NH2 to prepare asecondary amine derivative, and

2) reacting the substance prepared in step 1 with a L1 derivative whichis substituted with halogen.

This preparation method can be represented by Reaction scheme 3

Further, the present invention provides an organic electronic devicecomprising a first electrode, a second electrode, and at least oneorganic material layer interposed between the first electrode and thesecond electrode, wherein at least one organic material layer comprisesthe compound of formula 1.

The organic electronic device of the present invention can be preparedby usual methods and materials for preparing an organic electronicdevice, except that the above-described anthracene derivative are usedto form at least one organic material layer.

Hereinbelow, the organic light emitting device among organic electronicdevices using the anthracene derivative according to the presentinvention will be exemplified.

In one embodiment of the present invention, the organic light emittingdevice can have a structure comprising a first electrode, a secondelectrode, and organic material layers interposed therebetween. Theorganic material layer in the organic light emitting device of thepresent invention may be a monolayer structure comprising a singlelayer, or a multilayer structure comprising two or more layers includinga light emitting layer. If the organic material layer in the organiclight emitting device of the present invention has a multilayerstructure, it can has a structure in which a hole injecting layer, ahole transporting layer, a light emitting layer, an electrontransporting layer, and the like are laminated. However, the structureof the organic light emitting device is not limited thereto, and it canfurther comprise a fewer number of organic materials layer. For example,the structure of the organic light emitting device of the presentinvention can be that as shown FIG. 1. In FIG. 1, the numeral reference1 represents a substrate, 2 represents an anode, 3 represents a holeinjecting layer, 4 represents a hole transporting layer, 5 represents anorganic light emitting layer, 6 represents an electron transportinglayer, and 7 represents a cathode. The organic light emitting devicehaving the structure as shown in FIG. 1 is referred to as an organiclight emitting device having a forward structure. The present inventionis not limited thereto, and it also includes an organic light emittingdevice having a reverse structure. That is, the organic light emittingdevice of the present invention can have a structure in which asubstrate, a cathode, an electron transporting layer, an organic lightemitting layer, a hole transporting layer, a hole injecting layer and ananode are sequentially laminated.

If the organic light emitting device according to the present inventionhas a multilayer structure of the organic material layers, the compoundof formula 1 can be contained in a light emitting layer, a holetransporting layer, a hole transporting and light emitting layer, alight emitting and electron transporting layer, an electron transportinglayer, an electron transporting and/or injecting layer, and the like. Inthe present invention, the compound of formula 1 is particularlypreferably contained in an electron injecting and/or transporting layer,or a light emitting layer.

The organic light emitting device of the present invention can beprepared by usual methods and materials for preparing an organic lightemitting device, except that the anthracene derivative of formula 1 isused to form at least one of the organic material layers. For example,the organic light emitting device according to the present invention canbe prepared by depositing a metal, a metal oxide having conductivity oran alloy thereof on a substrate using a PVD (physical vapor deposition)process such as sputtering and e-beam evaporation to form an anode;forming an organic material layer comprising a hole injecting layer, ahole transporting layer, a light emitting layer and an electrontransporting layer on the anode; and depositing a material, which can beused as a cathode, thereon. Alternatively, an organic light emittingdevice can be prepared by sequentially depositing a cathode material, anorganic material layer, and an anode material on a substrate, thuspreparing the above-described organic light emitting device having areverse structure.

Further, the organic material layer can be prepared to have a fewernumber of layers, using a variety of polymeric materials, by means of asolvent process rather than a deposit process, such as spin coating, dipcoating, doctor blading, screen printing, ink jet printing, and heattransfer processes.

The anode material is preferably a material having a large work functionto facilitate hole injection usually to the organic material layers.Specific examples of the anode material which can be used in the presentinvention include metals such as vanadium, chromium, copper, zinc andgold, or an alloy thereof; metal oxides such as zinc oxide, indiumoxide, indium-tin oxide (ITO), and indium zinc oxide (IZO); acombination of a metal and an oxide, such as ZnO:Al and SnO₂:Sb;conductive polymers such as poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole andpolyaniline, but are not limited thereto.

The cathode material is preferably a material having a small workfunction to facilitate electron injecting usually to an organic materiallayer. Specific examples of the cathode material include metals such asmagnesium, calcium, sodium, potassium, titanium, indium, yttrium,lithium, gadolinium, aluminum, silver, tin and lead, and an alloythereof; and multilayered materials such as LiF/Al and LiO₂/Al, but arenot limited thereto.

The hole injecting material is a material facilitating hole injectionfrom an anode at low voltage. The HOMO (highest occupied molecularorbital) of the hole injecting material is preferably located betweenthe work function of the anode materials and the HOMO level of itsneighboring organic material layer. Specific examples of the holeinjecting material include organic materials of metal porphyrin,oligothiophene and arylamine series, organic materials of hexanitrilehexaazatriphenylene and quinacridone series, organic materials ofperylene series, and conductive polymers of anthraquinone, polyaniline,and polythiophene series, but are not limited thereto.

The hole transporting material is a material having high hole mobility,which can transfer holes from the anode or the hole injecting layertoward the light emitting layer. Specific examples thereof includeorganic materials of arylamine series, conductive polymers and blockcopolymers having both of the conjugated portions and the non-conjugatedportions, but are not limited thereto.

The light emitting material are a material capable of emitting visiblelight by accepting and recombining holes from the hole transportinglayer and electrons from the electron transporting layer, preferably amaterial having high quantum efficiency for fluorescence andphosphorescence. Specific examples thereof include 8-hydroxyquinolinealuminum complex (Alq₃); compounds of carbazole series; dimerized styrylcompounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds ofbenzoxazole, benzthiazole and benzimidazole series; polymers ofpoly(p-phenylenevinylene) (PPV) series; spiro compounds; andpolyfluorene and rubrene compounds, but are not limited thereto.

The electron transporting material is suitably a material having highelectron mobility, which can easily receive electrons from the cathodeand then transfer them to the light emitting layer. Specific examplesthereof include an Al complex of an 8-hydroxyquinoline aluminum complex;complexes including Alq₃; organic radical compounds; andhydroxyflavone-metal complexes, but are not limited thereto.

The organic light emitting device according to the present invention maybe of a front-sided, back-sided or double-sided light emission accordingto the materials used.

The compound according to the invention can also function in an organicelectronic device including an organic solar cell, an organicphotoconductor and an organic transistor, according to a principlesimilar to that applied to the organic light emitting device.

MODE FOR INVENTION

Hereinafter, preferable Examples are provided for the purpose of makingthe present invention more understandable. As such, Examples areprovided for illustrating the Examples, but the scope of the inventionis not limited thereto.

Preparative Example 1 1-1. Synthesis of Compound of the FollowingFormula 1-A

After 2,2′-dipyridylamine (5.0 g, 29 mmol) and 4-bromoiodobenzene (9.1g, 32.1 mmol) were dissolved in 70 ml of dimethyl acetamide (DMAC), CuCl(0.4 g, 2.9 mmol), 2,2′-dipyridyl (0.45 g, 2.9 mmol), and K₂CO₃ (8 g, 58mmol) were added, and the mixture was agitated at a room temperature for10 min and agitated at 160° C. for 8 hours. If the reaction wasfinished, the cooling was performed to a normal temperature, theextraction was performed with water and THF (tetrahydrofurane), waterwas removed with MgSO₄, THF was removed under reduced pressure, silicagel short column was performed by using hexane and THF, and theprecipitation was formed with water and ethanol (EtOH). The precipitatewas filtered to prepare the compound of formula 1-A (5.2 g, yield 54%)that was the white solid. MS: [M+H]⁺=327

1-2. Synthesis of Compound of the Following Formula 1-B

The compound of formula 1-B was prepared by using the same method as thesynthesis method of the compound of formula 1-A, except that3-bromoiodobenzene was used instead of 4-bromoiodobenzene in the courseof synthesizing the compound of formula 1-A of Preparation Example 1-1.MS: [M+H]⁺=327

1-3. Synthesis of Compounds of the Following Formulas 1-C and 1-D

After 2,2′-dipyridylamine (5.0 g, 29 mmol), 2-bromo-6-naphthol (5.4 g,24.2 mmol), and NaOt-Bu (7 g, 72.6 mmol) were put into toluene (250 mL),the mixture was heated to 50° C. Pd(P(t-Bu)₃)₂ (61.5 mg, 0.12 mmol) wasadded and then heated and agitated for 3 hours. The temperature wascooled to normal temperature, celite was added, and the agitation wasperformed for 10 min. The suspension solution was filtered by using afilter in which silica gel was provided by 1.5 cm. The filtrate wasdistilled under reduced pressure and recrystallized with ethanol (200mL) to obtain formula 1-C (3.8 g, yield 50%). MS: [M+H]⁺=314

After the compound of formula 1-C (8.4 g, 26.8 mmol) was dissolved indichloromethane, triethylamine (7.47 mL, 53.6 mmol) was added theretoand then agitated for 10 min. After the temperature was cooled to 0° C.,trifluoromethane sulfonic anhydride (4.4 mL, 40.2 mmol) was slowlyadded, the temperature was increased to normal temperature, and theagitation was performed for 1 hour. After the sodium hydrogen carbonateaqueous solution was added thereto, the water layer was removed andwater was removed with anhydrous magnesium sulfate. After the filtrationwas performed, the concentration was performed under reduced pressureand the recrystallization was performed with hexane to prepare thecompound of formula 1-D (10.8 g, yield 90%). MS: [M+H]⁺=446

1-4. Synthesis of Compound of the Following Formulas 1-E

The compound of formula 1-E was prepared by using the same method as thesynthesis method of the compound of formula 1-A, except thatphenyl-pyridin-2-yl-amine was used instead of 2,2′-dipyridylamine in thecourse of synthesizing the compound of formula 1-A of PreparationExample 1-1. MS: [M+H]⁺=326

1-5. Synthesis of Compounds of the Following Formulas 1-F and 1-G

The compound of formula 1-G was prepared by using the same method as thesynthesis method of the compound of formula 1-A, except that thecompound of formula 1-F was used instead of 2,2′-dipyridylamine in thecourse of synthesizing the compound of formula 1-A of PreparationExample 1-1. MS: [M+H]⁺=377

1-6. Synthesis of Compounds of the Following Formulas 1-H and 1-I

The compound of formula 1-I was prepared by using the same method as thesynthesis method of the compound of formula 1-A, except that thecompound of formula 1-H was used instead of 2,2′-dipyridylamine in thecourse of synthesizing the compound of formula 1-A of PreparationExample 1-1. MS: [M+H]⁺=427

Preparative Example 2 2-1. Synthesis of Compound of the FollowingFormula 2-A

2-Bromo-9,10-dinaphthylanthracene (5.00 g, 9.81 mmol),bis(pinacolato)diboron (2.75 g, 10.8 mmol) and potassium acetate (2.89g, 29.4 mmol) were suspended in dioxane (50 mL). To the suspension, wasadded palladium(diphenyl phosphinoferrocene)chloride (0.24 g, 0.3 mmol).The obtained mixture was stirred at 80° C. for about 6 hours, and thencooled to room temperature. The mixture was diluted with water (50 mL),and extracted from dichloromethane (3×50 mL). The organic extract wasdried over magnesium sulfate, and concentrated in vacuo. The crudeproduct washed with ethanol, and dried in vacuo to prepare a compound offormula 2-A (5.46 g, 92%), which is 9,10-dinaphthylanthracenyl-2-borate.MS: [M+H]⁺=557

2-2. Synthesis of Compound of the Following Formula 2-B

Carbazole (3.3 g, 20 mmol), 1-bromo-4-iodobenzene (3.0 mL, 24 mmol),potassium carbonate (K₂CO₃, 5.6 g, 41 mmol), copper iodide (CuI, 1.9 g,1.0 mmol), and 50 mL of xylene were refluxed under nitrogen atmosphere.The resultant was cooled to normal temperature, and the product wasextracted from ethyl acetate, the moisture was removed over anhydrousmagnesium sulfate (MgSO₄), and the solvent was removed under reducedpressure. The resultant was passed through as silica gel using a hexanesolvent to obtain a compound, and the solvent was removed under reducedpressure. The resultant was dried in vacuo to prepare a white solidcompound of formula 2-B (1.6 g, 25% yield). MS: [M+H]⁺=322

2-3. Synthesis of Compound of the Following Formula 2-C

The compound of formula 2-B (4.38 g, 13.2 mmol) was dissolved inanhydrous tetrahydrofuran (80 mL) under a nitrogen atmosphere. Thesolution was cooled to −78° C., n-butyl lithium (6.6 mL, 2.5 M hexanesolution) was slowly added over 10 minutes to the cooled solution, andthe solution was stirred at −78° C. for about 40 minutes.2-bromoanthraquinone compound (3.59 g, 5.5 mmol) was added to thereaction mixture, and the mixture was further stirred at −78° C. forabout 3 hours. The mixture was stirred at room temperature for about 1hour. To the mixture, an aqueous ammonium chloride solution (50 mL) wasadded. The organic layer was separated, and the aqueous layer wasextracted from diethyl ether (60 mL). The combined organic extract wasdried over magnesium sulfate, and concentrated under reduced pressure.The obtained solid was suspended in diethyl ether, stirred about 1 hour,filtered, and then dried to obtain a compound of formula 2-C (3.32 g,yield 73%), which is a dialcohol compound. MS [M+H]⁺=773

2-4. Synthesis of Compound of the Following Formula 2-D

The compound of formula 2-C (2.82 g, 3.65 mmol) was added to adispersion of acetic acid (60 mL), potassium iodide (3.32 g, 20 mmol)and hydrous sodium hypophosphite (3.52 g, 40 mmol) were added to thesuspension. The mixture was continuously stirred under reflux for about3 hours, and then cooled to room temperature. The mixture was filtered,washed with water, and then dried in vacuo to prepare a compound offormula 2-D (2.87 g, 90%). MS: [M+H]+=739

2-5. Synthesis of Compound of the Following Formula 2-E

A compound of formula 2-E was prepared in the same manner as in themethod for preparation of the compound of formula 2-A, except that acompound of formula 2-D was used instead of2-bromo-9,10-dinaphthylanthracene and bis(pinacolato)diboron in themethod for preparation of the compound of formula 2-A of PreparativeExample 2-1. MS: [M+H]⁺=787

2-6. Synthesis of Compound of the Following Formula 2-F

1-bromonaphthalene (34.8 g, 168.2 mmol) was dissolved in tetrahydrofuran(170 mL) and then cooled to −78° C., n-butyl lithium (67.3 mL, 168.2mmol) was slowly added thereto, and the agitation was performed for 1hour. 2-bromoanthraquinone (21 g, 73.1 mmol) was added thereto and thenheated to normal temperature, and the agitation was performed for 3hours. The saturated aqueous ammonium chloride solution was addedthereto, the water layer was removed, the drying was performed withanhydrous magnesium sulfate, the filtration was performed, and thedrying was performed under reduced pressure. The recrystallization wasperformed with ethyl ether and petroleum ether to prepare the compoundof formula 2-F (32.3 g, 82%). MS [M+H]⁺=544

2-7. Synthesis of Compound of the Following Formula 2-G

The compound of formula 2-F (32.3 g, 59.5 mmol), potassium iodide (29.6g, 178.4 mmol), sodium hypophosphite (38 g, 256.8 mmol) were added tothe acetic acid (40 ml), heated and agitated for 3 hours, and cooled tonormal temperature, the precipitate was filtered, the recrystallizationwas performed with ethanol to prepare a compound of formula 2-G (25.5 g,84%). MS: [M+H]⁺=509

2-8. Synthesis of Compound of the Following Formula 2-H

A compound of formula 2-H was prepared in the same manner as in themethod for synthesis of the compound of formula 2-A, except that acompound of formula 2-G was used instead of2-bromo-9,10-dinaphthylanthracene in the method for synthesis of thecompound of formula 2-A of Preparative Example 2-1. MS: [M+H]⁺=557

2-9. Synthesis of Compound of the Following Formula 2-I

A compound of formula 2-I was prepared in the same manner as in themethod for synthesis of the compound of formula 2-F, except that1-bromo-4-(2-naphthyl)benzene was used instead of 1-bromonaphthalene inthe method for synthesis of the compound of formula 2-F of PreparativeExample 2-6. MS: [M+H]⁺=696

2-10. Synthesis of Compound of the Following Formula 2-J

A compound of formula 2-J was prepared in the same manner as in themethod for synthesis of the compound of formula 2-G, except that thecompound of formula 2-I was used instead of the compound of formula 2-Fin the method for synthesis of the compound of formula 2-G ofPreparative Example 2-7. MS: [M+H]⁺=661

2-11. Synthesis of Compound of the Following Formula 2-K

A compound of formula 2-K was prepared in the same manner as in themethod for synthesis of the compound of formula 2-A, except that thecompound of formula 2-J was used instead of2-bromo-9,10-dinaphthylanthracene in the method for synthesis of thecompound of formula 2-A of Preparative Example 2-1. MS: [M+H]⁺=709

Preparative Example 3 3-1. Synthesis of Compound of the FollowingFormula 1-11

After 2,2′-dipyridylamine (5.0 g, 29 mmol),2-bromo-9,10-dinaphthylanthracene (12.3 g, 24.2 mmol), and NaOt-Bu (7 g,72.6 mmol) were put into toluene (250 mL), the mixture was heated to 50°C. Pd(P(t-Bu)₃)₂ (61.5 mg, 0.12 mmol) was added and then heated andagitated for 3 hours. The temperature was cooled to normal temperature,celite was added, and the agitation was performed for 10 min. Thesuspension solution was filtered by using a filter in which silica gelwas provided by 1.5 cm. The filtrate was distilled under reducedpressure and recrystallized with ethanol (200 mL) to obtain a compoundof formula 1-11 (10.1 g, yield 70%). MS: [M+H]⁺=600

3-2. Synthesis of Compound of the Following Formula 1-13

A compound of formula 1-13 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-11, except that thecompound of formula 2-G was used instead of2-bromo-9,10-dinaphthylanthracene in the method for synthesis of thecompound of formula 1-11 of Preparative Example 3-1. MS: [M+H]⁺=600

3-3. Synthesis of Compound of the Following Formula 1-21

A compound of formula 1-21 was prepared in the same mariner as in themethod for synthesis of the compound of formula 1-11, except that thecompound of formula 3-A was used instead of 2,2′-dipyridylamine in themethod for synthesis of the compound of formula 1-11 of PreparativeExample 3-1. MS: [M+H]⁺=649

3-4. Synthesis of Compound of the Following Formula 1-75

After 2-aminopyridine (2.7 g, 29 mmol),2-bromo-9,10-dinaphthylanthracene (12.3 g, 24.2 mmol), NaOt-Bu (7 g,72.6 mmol) were put into toluene (250 mL), the mixture was heated to 50°C. Pd(P(t-Bu)₃)₂ (61.5 mg, 0.12 mmol) was added and then heated andagitated for 3 hours. The temperature was cooled to normal temperature,celite was added, and the agitation was performed for 10 min. Thesuspension solution was filtered by using a filter in which silica gelwas provided by 1.5 cm. The filtrate was distilled under reducedpressure and recrystallized with ethanol (200 mL) to obtain the compoundof formula 3-B (7.6 g, yield 60%). MS: [M+H]⁺=523

After the compound of formula 3-B (15.1 g, 29 mmol), the compound offormula 2-D (17.9 g, 24.2 mmol), and NaOt-Bu (7 g, 72.6 mmol) were putinto toluene (250 mL), the mixture was heated to 50° C. Pd(P(t-Bu)₃)₂(61.5 mg, 0.12 mmol) was added and then heated and agitated for 3 hours.The temperature was cooled to normal temperature, celite was added, andthe agitation was performed for 10 min. The suspension solution wasfiltered by using a filter in which silica gel was provided by 1.5 cm.The filtrate was distilled under reduced pressure and recrystallizedwith ethanol (200 mL) to obtain the compound of formula 1-75 (14.5 g,yield 50%). MS: [M+H]⁺=1198

3-5. Synthesis of Compound of the Following Formula 1-91

After the compound of formula 2-A (3.5 g, 6.3 mmol) and the compound(2.2 g, 6.9 mmol) of formula 1-E were completely dissolved intetrahydrofurnae (100 ml), 2M potassium carbonate aqueous solution wasadded thereto, tetrakistriphenylphosphinopalladium (155 mg, 0.013 mmol)was added thereto, and the heating and the agitation were performed for5 hours. The temperature was cooled to a normal temperature, the waterlayer was removed, the drying was performed with anhydrous magnesiumsulfate, the concentration was performed under reduced pressure, thecolumn was performed so that the ratio of tetrahydrofurane:hexane was inthe range of 1:6 to prepare the compound of formula 1-91 (2.8 g, 66%).MS: [M+H]⁺=675

3-6. Synthesis of Compound of the Following Formula 1-101

A compound of formula 1-101 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-91, except that thecompound of formula 1-A was used instead of the compound of formula 1-Ein the method for synthesis of the compound of formula 1-91 ofPreparative Example 3-5. MS: [M+H]⁺=676

3-7. Synthesis of Compound of the Following Formula 1-103

A compound of formula 1-103 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-101, except that thecompound of formula 2-H was used instead of the compound of formula 2-Ain the method for synthesis of the compound of formula 1-101 ofPreparative Example 3-6. MS: [M+H]⁺=676

3-8. Synthesis of Compound of the Following Formula 1-106

A compound of formula 1-106 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-101, except that thecompound of formula 2-K was used instead of the compound of formula 2-Ain the method for synthesis of the compound of formula 1-101 ofPreparative Example 3-6. MS: [M+H]⁺=829

3-9. Synthesis of Compound of the Following Formula 1-171

A compound of formula 1-171 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-101, except that thecompound of formula 3-C was used instead of the compound of formula 1-Ain the method for synthesis of the compound of formula 1-101 ofPreparative Example 3-6. MS: [M+H]⁺=834

3-10. Synthesis of Compound of the Following Formula 1-191

A compound of formula 1-191 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-101, except that thecompound of formula 1-D was used instead of the compound of formula 1-Ain the method for synthesis of the compound of formula 1-101 ofPreparative Example 3-6. MS: [M+H]⁺=726

3-11. Synthesis of Compound of the Following Formula 1-193

A compound of formula 1-193 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-191, except that thecompound of formula 2-H was used instead of the compound of formula 2-Ain the method for synthesis of the compound of formula 1-191 ofPreparative Example 3-10. MS: [M+]⁺=726

3-12. Synthesis of Compound of the Following Formula 1-302

A compound of formula 1-302 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-11, except that thecompound of formula 1-F was used instead of 2,2′-dipyridylamine in themethod for synthesis of the compound of formula 1-11 of PreparativeExample 3-1. MS: [M+H]⁺=650

3-13. Synthesis of Compound of the Following Formula 1-303

A compound of formula 1-303 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-11, except that thecompound of formula 1-H was used instead of 2,2′-dipyridylamine in themethod for synthesis of the compound of formula 1-11 of PreparativeExample 3-1. MS: [M+H]⁺=700

3-14. Synthesis of Compound of the Following Formula 1-314

A compound of formula 1-314 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-91, except that thecompound of formula 1-G was used instead of the compound of formula 1-Ein the method for synthesis of the compound of formula 1-91 ofPreparative Example 3-5. MS: [M+H]⁺=726

3-15. Synthesis of Compound of the Following Formula 1-315

A compound of formula 1-315 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-91, except that thecompound of formula 1-I was used instead of the compound of formula 1-Ein the method for synthesis of the compound of formula 1-91 ofPreparative Example 3-5. MS: [M+H]⁺=776

3-16. Synthesis of Compound of the Following Formula 1-319

A compound of formula 1-319 was prepared in the same manner as in themethod for synthesis of the compound of formula 1-91, except that thecompound of formula 3-D was used instead of the compound of formula 1-Ein the method for synthesis of the compound of formula 1-91 ofPreparative Example 3-5. MS: [M+H]⁺=747

Preparative Example 4 4-1. Synthesis of Compound of the FollowingFormula 2-11

After 2,2′-dipyridylamine (17.7 g, 103.7 mmol),2,6-dibromo-9,10-bis(2-naphthyl)anthracene (25.4 g, 43.2 mmol), andNaOt-Bu (12.5 g, 129.6 mmol) were put into toluene (346 mL), the mixturewas heated to 50° C. Pd(P(t-Bu)₃)₂ (220.5 mg, 0.43 mmol) was added andthen heated and agitated for 3 hours. The temperature was cooled tonormal temperature, celite was added, and the agitation was performedfor 10 min. The suspension solution was filtered by using a filter inwhich silica gel was provided by 1.5 cm. The filtrate was distilledunder reduced pressure and recrystallized with ethanol (200 mL) toobtain a compound of formula 2-11 (10 g, yield 30%). MS: [M+H]⁺=769

4-2. Synthesis of Compound of the Following Formula 2-13

A compound of formula 2-13 was prepared in the same manner as in themethod for synthesis of the compound of formula 2-11, except that2,6-dibromo-9,10-bis(1-naphthyl)anthracene was used instead of2,6-dibromo-9,10-bis(2-naphthyl)anthracene in the method for synthesisof the compound of formula 2-11 of Preparative Example 4-1. MS:[M+H]⁺=769

4-3. Synthesis of Compound of the Following Formula 2-21

A compound of formula 2-21 was prepared in the same manner as in themethod for synthesis of the compound of formula 2-11, except that thecompound of formula 3-A was used instead of 2,2′-dipyridylamine in themethod for synthesis of the compound of formula 2-11 of PreparativeExample 4-1. MS: [M+H]⁺=867

4-4. Synthesis of Compound of the Following Formula 2-71

A compound of formula 2-71 was prepared in the same manner as in themethod for synthesis of the compound of formula 2-11, except that thecompound of formula 1-F was used instead of 2,2′-dipyridylamine in themethod for synthesis of the compound of formula 2-11 of PreparativeExample 4-1. MS: [M+H]⁺=869

4-5. Synthesis of Compound of the Following Formula 2-81

After the compound of formula 4-A (2.2 g, 3.2 mmol) and the compound(2.2 g, 6.9 mmol) of formula 1-E were completely dissolved intetrahydrofurnae (100 ml), 2M potassium carbonate aqueous solution wasadded thereto, tetrakistriphenylphosphinopalladium (155 mg, 0.013 mmol)was added thereto, and the heating and the agitation were performed for5 hours. The temperature was cooled to a normal temperature, the waterlayer was removed, the drying was performed with anhydrous magnesiumsulfate, the concentration was performed under reduced pressure, thecolumn was performed so that the ratio of tetrahydrofurane:hexane was inthe range of 1:6 to prepare the compound of formula 2-81 (1.3 g, 45%).MS: [M+H]+=919

4-6. Synthesis of Compound of the Following Formula 2-91

A compound of formula 2-91 was prepared in the same manner as in themethod for synthesis of the compound of formula 2-81, except that thecompound of formula 1-A was used instead of the compound of formula 1-Ein the method for synthesis of the compound of formula 2-81 ofPreparative Example 4-5. MS: [M+H]⁺=921

4-7. Synthesis of Compound of the Following Formula 2-141

A compound of formula 2-141 was prepared in the same manner as in themethod for synthesis of the compound of formula 2-81, except that thecompound of formula 1-G was used instead of the compound of formula 1-Ein the method for synthesis of the compound of formula 2-81 ofPreparative Example 4-5. MS: [M+H]⁺=1021

Experimental Example 1

A glass substrate on which a thin film of ITO (indium tin oxide) wascoated to a thickness of 1500 Å was immersed in distilled water having adetergent dissolved therein to wash the substrate with ultrasonic waves.The detergent as used herein was a product commercially available fromFisher Co. and the distilled water was one which had been twice filteredby using a filter commercially available from Millipore Co. ITO waswashed for 30 minutes, and then washing with ultrasonic waves wasrepeated twice for 10 minutes by using distilled water. After thecompletion of washing with distilled water, washing with ultrasonicwaves was carried out by using solvents such as isopropyl alcohol,acetone and methanol. The resultant product was dried, and thentransported to a plasma washing machine. Using an oxygen plasma, thesubstrate was washed for 5 minutes and then transported to a vacuumdepositing machine.

On the ITO transparent electrode thus prepared, hexanitrilehexaazatriphenylene (HAT) of the following formula was coated tothicknesses of 500 Å by thermal vacuum deposition to form a holeinjecting layer.

4,4′-Bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 Å) of thefollowing formula, which is a hole transporting material, was coated onthe hole injecting layer by vacuum deposition, to form a holetransporting layer.

Then, Alq₃ (aluminum tris(8-hydroxyquinoline)) of the following formulawas coated to a thickness of 300 Å on the hole transporting layer byvacuum deposition to form a light emitting layer.

The compound of formula 1-21 as prepared in Preparative Example 3 wascoated to a thickness of 200 Å on the light emitting layer by vacuumdeposition to form an electron injecting and transporting layer.

Lithium fluoride (LiF) and aluminum were sequentially deposited on theelectron injecting and transporting layer to thicknesses of 12 Å and2000 Å respectively, to form a cathode.

In the above process, the deposition rate of the organic material wasmaintained at 0.4 to 0.7 Å/sec and the deposition rate of lithiumfluoride was maintained at 0.3 Å/sec and the deposition rate of aluminumwas maintained at 2 Å/sec, respectively. The degree of vacuum upondeposition was maintained at 2×10⁻⁷ to 5×10⁻⁸ torr.

When a forward electric field of 5.6 V was applied to the organic lightemitting device as prepared above, green light emission was observedwith x=0.32 and y=0.55 based on the 1931 CIE color coordinate at acurrent density of 50 mA/cm². When a forward electric field of 6.4 V wasapplied, green light emission of 2.6 cd/A was observed at a currentdensity of 100 mA/cm².

Experimental Example 2

On the ITO electrode as prepared as in Example 1, hexanitrilehexaazatriphenylene (500 Å),4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 Å), Alq₃ (300Å), and the compound 1-101 (200 Å) were sequentially coated by thermalvacuum deposition, to form a hole injecting layer, a hole transportinglayer, a light emitting layer, and an electron transporting layer inthis order.

Lithium fluoride (LiF) and aluminum were sequentially deposited on theelectron transporting layer to thicknesses of 12 Å and 2000 Årespectively, to form a cathode, thereby preparing an organic lightemitting device.

In the above process, the deposition rate of the organic material wasmaintained at 0.4 to 0.7 Å/sec and the deposition rate of lithiumfluoride was maintained at 0.3 Å/sec and the deposition rate of aluminumwas maintained at 2 Å/sec, respectively. The degree of vacuum upondeposition was maintained at 2×10⁻⁷ to 5×10⁻⁸ torr.

When a forward electric field of 4.1 V was applied to the organic lightemitting device as prepared above, green light emission was observedwith x=0.33 and y=0.56 based on the 1931 CIE color coordinate at acurrent density of 50 mA/cm². When a forward electric field of 5.0 V wasapplied, green light emission of 2.0 cd/A was observed at a currentdensity of 100 mA/cm².

Experimental Example 3

On the ITO electrode as prepared as in Example 1, hexanitrilehexaazatriphenylene (500 Å),4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 Å), and thecompound I-191 (400 Å) were sequentially coated by thermal vacuumdeposition, to form a hole injecting layer, a hole transporting layer,and a light emitting and electron transporting layer in this order.

Lithium fluoride (LiF) and aluminum were sequentially deposited on thelight emitting and electron transporting layer to thicknesses of 12 Åand 2000 Å respectively, to form a cathode, thereby preparing an organiclight emitting device.

In the above process, the deposition rate of the organic material wasmaintained at 0.4 to 0.7 Å/sec and the deposition rate of lithiumfluoride was maintained at 0.3 Å/sec and the deposition rate of aluminumwas maintained at 2 Å/sec, respectively. The degree of vacuum upondeposition was maintained at 2×10⁻⁷ to 5×10⁻⁸ torr.

When a forward electric field of 4.3 V was applied to the organic lightemitting device as prepared above, green light emission was observedwith x=0.33 and y=0.58 based on the 1931 CIE color coordinate at acurrent density of 50 mA/cm². When a forward electric field of 5.2 V wasapplied, green light emission of 2.1 cd/A was observed at a currentdensity of 100 mA/cm².

Experimental Example 4

On the ITO electrode as prepared as in Example 1, hexanitrilehexaazatriphenylene (500 Å),4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 Å), Alq₃ (300Å), the compound of formula 1-315 (200 Å), lithium fluoride (LiF) (12 Å)were sequentially coated by thermal vacuum deposition, to form a holeinjecting layer, a hole transporting layer, a light emitting layer, anelectron transporting layer and an electron injecting layer in thisorder. Aluminum was deposited thereon to a thickness of 2000 Å to form acathode, thereby preparing an organic light emitting device.

When a forward electric field of 4.2 V was applied to the organic lightemitting device as prepared above, green light emission was observedwith x=0.32 and y=0.56 based on the 1931 CIE color coordinate at acurrent density of 50 mA/cm². When a forward electric field of 5.1 V wasapplied, green light emission of 2.1 cd/A was observed at a currentdensity of 100 mA/cd.

Experimental Example 5

On the ITO electrode as prepared as in Example 1, hexanitrilehexaazatriphenylene (500 Å),4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 Å), Alq₃ (300Å), the compound of formula 2-91 (200 Å), and lithium fluoride (LiF) (12Å) were sequentially coated by thermal vacuum deposition, to form a holeinjecting layer, a hole transporting layer, a light emitting layer, anelectron transporting layer and an electron injecting layer in thisorder. Aluminum was deposited thereon to a thickness of 2000 Å to form acathode, thereby preparing an organic light emitting device.

When a forward electric field of 4.3 V was applied to the organic lightemitting device as prepared above, green light emission was observedwith x=0.33 and y=0.58 based on the 1931 CIE color coordinate at acurrent density of 50 mA/cm². When a forward electric field of 5.1 V wasapplied, green light emission of 2.0 cd/A was observed at a currentdensity of 100 mA/cm².

Comparative Example 1

On the ITO electrode as prepared as in Example 1, hexanitrilehexaazatriphenylene (500 Å),4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 Å), Alq₃ (300Å), the electron transporting substance represented by the followingformula (200 Å), and lithium fluoride (LiF) (12 Å) were sequentiallycoated by thermal vacuum deposition, to form a hole injecting layer, ahole transporting layer, a light emitting layer, an electrontransporting layer and an electron injecting layer in this order.Aluminum was deposited thereon to a thickness of 2000 Å to form acathode, thereby preparing an organic light emitting device.

When a forward electric field of 4.3 V was applied to the organic lightemitting device as prepared above, green light emission was observedwith x=0.33 and y=0.56 based on the 1931 CIE color coordinate at acurrent density of 50 mA/cm². When a forward electric field of 6.8 V wasapplied, green light emission of 2.4 cd/A was observed at a currentdensity of 100 mA/cd.

Comparative Example 2

On the ITO electrode as prepared as in Example 1, hexanitrilehexaazatriphenylene (500 Å),4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 Å), Alq₃ (300Å), the electron transporting substance-1 represented by the followingformula (200 Å), and lithium fluoride (LiF) (12 Å) were sequentiallycoated by thermal vacuum deposition, to form a hole injecting layer, ahole transporting layer, a light emitting layer, an electrontransporting layer and an electron injecting layer in this order.Aluminum was deposited thereon to a thickness of 2000 Å to form acathode, thereby preparing an organic light emitting device.

When a forward electric field of 4.3 V was applied to the organic lightemitting device as prepared above, green light emission was observedwith x=0.34 and y=0.58 based on the 1931 CIE color coordinate at acurrent density of 50 mA/cm². When a forward electric field of 7.8 V wasapplied, green light emission of 1.4 cd/A was observed at a currentdensity of 100 mA/cm².

1. An anthracene derivative that is represented by the following formula1:

wherein R1 and R2 may be the same as or different from each other, andare independently selected from the group consisting of a C₆ to C₄₀ arylgroup which is unsubstituted or substituted with at least one selectedfrom the group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C₆ to C₄₀ aryl group, a C₃ to C₄₀ heteroarylgroup and an arylamine group; a C₃ to C₄₀ heteroaryl group which isunsubstituted or substituted with at least one selected from the groupconsisting of halogen, an amino group, a nitrile group, a nitro group, aC₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxygroup, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group,a C₆ to C₄₀ aryl group and a C₃ to C₄₀ heteroaryl group; and a C₆ to C₄₀amino group which is unsubstituted or substituted with at least oneselected from the group consisting of halogen, an amino group, a nitrilegroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₁ to C₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ toC₄₀ heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group, at least one of R3 and R4 is represented by thefollowing formula 2:

wherein X is selected from the group consisting of N, P and P═O, Y isselected from the group consisting of C—H and N, L₁ is a direct bond; oris selected from the group consisting of a C₂ to C₄₀ alkenylene groupwhich is unsubstituted or substituted with at least one selected fromthe group consisting of a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₁ to C₄₀ alkoxy group, a C₆ to C₄₀aryl group, and a C₃ to C₄₀ heteroaryl group; a C₆ to C₄₀ arylene groupwhich is unsubstituted or substituted with at least one selected fromthe group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group; C₅ to C₄₀ heteroarylene group which is unsubstitutedor substituted with at least one selected from the group consisting ofhalogen, an amino group, a nitrile group, a nitro group, a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀aryl group and a C₃ to C₄₀ heteroaryl group; and a C₆ to C₄₀ arylaminegroup which is unsubstituted or substituted with at least one selectedfrom the group consisting of a C₁ to C₄₀ alkyl group, a C₂ to C₄₀alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, aC₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group, R5, R6, R7, R8, R9, R10, R11, and R12 may be the sameas or different from each other, and are selected from the groupconsisting of hydrogen; a silicon group which is unsubstituted orsubstituted with at least one selected from the group consisting ofhalogen, an amino group, a nitrile group, a nitro group, a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀aryl group and a C₃ to C₄₀ heteroary group; a C₂ to C₄₀ alkyl groupwhich is unsubstituted or substituted with at least one selected fromthe group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group; a C₃ to C₄₀ cycloalkyl group which is unsubstituted orsubstituted with at least one selected from the group consisting ofhalogen, an amino group, a nitrile group, a nitro group, a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀aryl group and a C₃ to C₄₀ heteroaryl group; a C₂ to C₄₀ alkenyl groupwhich is unsubstituted or substituted with at least one selected fromthe group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group; a C₁ to C₄₀ alkoxy group which is unsubstituted orsubstituted with at least one selected from the group consisting ofhalogen, an amino group, a nitrile group, a nitro group, a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀aryl group and a C₃ to C₄₀ heteroaryl group; an amino group which isunsubstituted or substituted with at least one selected from the groupconsisting of halogen, an amino group, a nitrile group, a nitro group, aC₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxygroup, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group,a C₆ to C₄₀ aryl group and a C₃ to C₄₀ heteroaryl group; a C₆ to C₄₀aryl group which is unsubstituted or substituted with at least oneselected from the group consisting of halogen, an amino group, a nitrilegroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₁ to C₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ toC₄₀ heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group; and a C₃ to C₄₀ heteroaryl group which isunsubstituted or substituted with at least one selected from the groupconsisting of halogen, an amino group, a nitrile group, a nitro group, aC₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxygroup, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group,a C₆ to C₄₀ aryl group and a C₃ to C₄₀ heteroaryl group, or are bondedwith an adjacent group to form an aliphatic, aromatic, heteroaliphatic,or heteroaromatic condensed ring, or to form a spiro bond, and when anyone of R3 and R4 is represented by formula 2, the other is selected fromthe group consisting of hydrogen; a C₆ to C₄₀ aryl group which isunsubstituted or substituted with at least one selected from the groupconsisting of halogen, an amino group, a nitrile group, a nitro group, aC₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxygroup, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group,a C₆ to C₄₀ aryl group, a C₃ to C₄₀ heteroaryl group and an arylaminegroup; a C₃ to C₄₀ heteroaryl group which is unsubstituted orsubstituted with at least one selected from the group consisting ofhalogen, an amino group, a nitrile group, a nitro group, a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃to C₄₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀aryl group and a C₃ to C₄₀ heteroaryl group; and a C₆ to C₄₀ amino groupwhich is unsubstituted or substituted with at least one selected fromthe group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group.
 2. The anthracene derivative as set forth in claim 1,wherein R1 and R2 of formula 1 are the same aryl groups.
 3. Theanthracene derivative as set forth in claim 1, wherein R1 and R2 offormula 1 are the same heteroaryl groups.
 4. The anthracene derivativeas set forth in claim 1, wherein R1 and R2 of formula 1 are the aminogroups substituted with the same C6˜C40 aryl groups or the same C3˜C40heteroaryl groups.
 5. The anthracene derivative as set forth in claim 1,wherein R1 and R2 of formula 1 are independently selected from the groupconsisting of the following structural formulae:

wherein Z1 to Z3 are the same as or different from each other, and areindependently selected from the group consisting of hydrogen; a C₆ toC₄₀ aryl group which is unsubstituted or substituted with at least oneselected from the group consisting of halogen, an amino group, a nitrilegroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₁ to C₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ toC₄₀ heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group; a C₃ to C₄₀ heteroaryl group which is unsubstituted orsubstituted with at least one selected from the group consisting ofhalogen, an amino group, a nitrile group, a nitro group, a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ to C₄₀ alkoxy group, a C₃to C₁₀ cycloalkyl group, a C₃ to C₄₀ heterocycloalkyl group, a C₆ to C₄₀aryl group and a C₃ to C₄₀ heteroaryl group; and a C₆ to C₄₀ amine groupwhich is unsubstituted or substituted with at least one selected fromthe group consisting of halogen, an amino group, a nitrile group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₁ toC₄₀ alkoxy group, a C₃ to C₄₀ cycloalkyl group, a C₃ to C₄₀heterocycloalkyl group, a C₆ to C₄₀ aryl group and a C₃ to C₄₀heteroaryl group.
 6. The anthracene derivative as set forth in claim 1,wherein L₁ of formula 2 is any one selected from a direct bond, anunsubstituted C₆˜C₄₀ arylene group, and an unsubstituted C₅˜C₄₀heteroarylene group.
 7. The anthracene derivative as set forth in claim1, wherein R5, R6, R7, R8, R9, R10, R11, and R12 of formula 2 are allhydrogen or at least one of R5, R6, R7, R8, R9, R10, R11, and R12 is aC₆˜C₄₀ aryl group that is unsubstituted or substituted with a C₁˜C₄₀alkyl group or a C₆˜C₄₀ aryl group.
 8. The anthracene derivative as setforth in claim 1, wherein the alkyl group is selected from the groupconsisting of a methyl group, an ethyl group, a propyl group, anisopropyl group, a butyl group, a t-butyl group, a pentyl group, a hexylgroup and a heptyl group; the cycloalkyl group is a cyclopentyl group ora cyclohexyl group; the alkenyl group is an alkenyl group in which anaryl group of a stilbenzyl group or a styrenyl group is substituted; thealkoxy group is an alkoxy group having 1 to 40 carbon atoms; the arylgroup is selected from the group consisting of a phenyl group, anaphthyl group, an anthracenyl group, a biphenyl group, a pyrenyl group,a perylenyl group, and a derivative thereof; the aryl amine group isselected from the group consisting of a phenylamine group, anaphthylamine group, a biphenylamine group, an anthracenylamine group, a3-methyl-phenylamine group, a 4-methyl-naphthylamine group, a2-methyl-biphenylamine group, a 9-methyl-anthracenylamine group, adiphenylamine group, a phenylnaphthylamine group, a ditolylamine group,a phenyltolylamine group, a carbazole group and a triphenylamine group;the heterocyclic group is selected from the group consisting of apyridyl group, a bipyridyl group, a triazine group, an acridyl group, athiophene group, a puran group, an imidazole group, an oxazole group, athiazole group, a triazole group, a quinolinyl group, and anisoquinoline group; and the halogen group is selected from the groupconsisting of fluorine, chlorine, bromine, and iodine.
 9. An organicelectronic device comprising a first electrode, a second electrode, andat least one organic material layer interposed between the firstelectrode and the second electrode, wherein at least one of the organicmaterial layers comprises the anthracene derivative of formula 1according to claim
 1. 10. The organic electronic device as set forth inclaim 9, wherein the organic electronic device is selected from thegroup consisting of an organic light emitting device, an organic solarcell, an organic photoconductor (OPC) drum and an organic transistor.11. The organic electronic device as set forth in claim 9, wherein theorganic electronic device is an organic light emitting device.
 12. Theorganic electronic device as set forth in claim 11, wherein the organiclight emitting device has a forward structure in which an anode, atleast one organic material layer, and a cathode are sequentiallylaminated on a substrate.
 13. The organic electronic device as set forthin claim 11, wherein the organic light emitting device has a reversestructure in which a cathode, at least one organic material layer, andan anode are sequentially laminated on a substrate.
 14. The organicelectronic device as set forth in claim 11, wherein the organic lightemitting device comprises the anthracene derivative of formula 1 whichis included in the organic material layer comprising one or moreselected from a hole injecting layer, a hole transporting layer, a lightemitting layer, an electron injecting and an electron transportinglayer.
 15. The organic electronic device as set forth in claim 9,wherein the organic material layer comprises a light emitting layer, andthe light emitting layer comprises the anthracene derivative offormula
 1. 16. The organic electronic device as set forth in claim 9,wherein the organic material layer comprises an electron transportinglayer or electron injecting layer, and the electron transporting layeror the electron injecting layer comprises the anthracene derivative offormula 1.